When you're the boss, you can do whatever you want—but you better be right. Peter Chiarelli took over the Edmonton Oilers just weeks before the Connor McDavid draft, a golden time for the Oilers brand. New arena, new saviour, new future and finally, after all the searing pain that came from a decade of losing, a clear path to the promised land.

No one is guaranteed Stanley, but winning that 2015 lottery brought enormous promise to the NHL's northernmost city. With it came pressure and there was much work to do, Chiarelli casting about to see what useful pieces he could trade in order to fast-track success. When you're the boss, you can do what you want—but you better be right.

November 3, 2013: The dictionary defines nadir as “the lowest or most unsuccessful point in a situation” and Oiler fans know the feeling. The only real question is “which one?” Is it the 2009-10? Is it the 2011-12? Is it the 2013? Or, incredibly, is it now?

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